Aromatic ketone and process of making same.



NO- 830,044. PATENTED SEPT. 4, 19.06.

H. S. BLAGKMORE.

AROMATIG KETONE AND PROCESS 0F' MAKING SAME. APPLIGATION FILED 001213, 1902.

l v Al is provided witha detachable head E ,hav-

TED STATES PATENT OFFICE.

HENRY SPENCER BLACKMORE, OF MOUNT VERNON, NEW YORK.

AROMATIC KETONE AND PROCESS OF MAKING SAME.

Specification of Letters Patent.

Application filed October 13,1902. -Serial No.'127,132. (Specimens.)

To a/ZZ whom it may concern.:

Be it known that I, HENRY SPENCER BLACEM'OEE, a citizen of theUnited States, residing at Mount Vernon, in the county of Westchester and State of New York, have invented certain new and useful Improvements in Pyroxylinl Solvents and Aromatic Ketones, of which the following is a specification.

The object of my invention is to' produce aromatic ketones for employment as solvents for pyroxylin and for other purposes; and the process consists in oxidizing aromatic hydrocarbons of the general formula (C5H)n while maintaining the temperature below the dissociating-point of the ketone desired.Y

My invention relates more especially to the production of solid ketones, such as the keto derivative of tetrahydro-methylpro yl benzene, which may be isolated by sub imation after oxidation of the hydrocarbon, such as correspond to the general formula (051118), but is not confined to this particular class of aromatic ketones, but may include aromatic liquid ketones, which are often produced by the union or condensation of complex ketones, any one of which may. exist individually as a solid, but on their union produce a liquid having similar properties, such as camphor and menthone.

In carrying out my invention for the production vof the keto derivative of tetrahydromethylpropyl benzene, (C3H7.C5H,CO.CH3,) which 1s an excellent solvent in its liquefied condition for pyroxylin, I roceed as follows, reference being had to t e accompan g drawings, which illustrate a preferred orm of ap aratus which I employ for the purpose.

Re erring to the drawings, Figure 1 is a vertical longitudinal section of my apparatus. Fig. 2 is an enlar ed vertical section showing the electric diap agms and the connection of the transforming-chamber, and Fig. 3 .is a cross-,section of one of the rings and electric connection of the transforming-chamber and an'lectric gauze diaphragm connected therewit i l r Similar letters refer to corresponding parts in the several views.

The letter A-de'signates a transformingchamber of cylindrical or other `form provided at its top with an clbowB and pipe C, the latter connected with a jacketed con'- denser D iny anydesired \airtightmanner. The lower end of the transforming-chamber ing a central stuffing-box or screw-threaded `plug F, of insulating material, connected therewith and in which is fitted a rod or electric connection G, the upper portion of which is formed in sections having screw-threaded connections, as shown at a a a in-Fig. 2. The transforming-chamber A, like the electric connection G, is partly composed of sections, as shown at b b b, (see Flgs. 1 and 2,)

the said sections being joined together by the threaded ends c c c. A series of ,metallicgauze diaphragms d are arranged within the transforming chamber A, the said diaphragms being securely held in relative positions by the abutting shoulders of the screwthreaded ends of the transforming-chamber rings and of the central connection thereof.

Patented Sept. 4, 1906.

The upper and lower diaphragms d and d are arranged'in several thicknesses, forming a heat-absorber and flash-preventer, and insulated fronr the electrical connection G, as shown at e c', for the purposes hereinafter fully described. Pee -holes f( f having mica fronts or covers h', are ocated at the opposite sides of the combustion or transforming compartments A to enable the attendant to view the interior thereof and provide for regulating the apparatus as occasion may require.

The letters i and fi. and t designate electric. wires, which are respectively connected with the electric conductor G and the walls of the transforming-chamber A by ordinary means.

The lower part of the transforming-chamber is rovided horizontally with a ipe-section having a detachable end or ead h, within which is tightly fitted a tube l, the latter provided With a T-head l and an inletpipe m, while-within the stem of the T-'head and the tubel is arranged a pipe n for the y purposes hereinafter fu ly specified.

In the operation of my invention for the .production oftheketo derivative of tetrahy- IOO dro-methylpropyl benzene I take dipentene (C5H)2 and vaporize it by means of heat or,

a current of heatedgas and convey it into .a transforming-chamber of `the apparatus described throughthe .pipe n. I then introduce carbon dioxid (00,) through the pipe fm,

regulating it to about equivalent proportions r' to produce by condensationand oxidation the; ketojderivativecof tetrahydro-methylpropyl benzene and carbonio oxid, as hereinafteriset-forth. Asthe dipentene vapor and IIO carbon dioxid enter the apparatus they bel Y the chamber A, then pass up through an in- -bein sulated-gauze ash-preventer d into the transf rming-compartment A. A current of elec ricity is then'passed through the connections 'i i fi, the same passing through theV diaphragms d d, heating them, in'proportion to the strength of the current, either low red or to whiteness, as desired, thetemperature somewhat gaged by ,the color of the diap agm, which can be observed through the lmica-closed peep-holesff. As the' mixture of dipentene vapor and carbon dioxid comes in contact with the-heated gauze diaphragms a reaction takes place, which may be illustrated by the following chemical formula or equation:

The current' of vapor and gas introduced passing rapidly through the apparatus carries the product of reaction quickly through and away from the heated gauze diaphragms and through the flash-preventer d, which consists of a number of layers of gauze insulated, as before described, from the central conductor and which also acts as a strainer or absorbent of the excess of heatand conveys it away, thus preventing the temperature from rising above the dissociatin point of the product produced. The keto erivative of tetrahydro-methylpropyl benzene product produced is conveyed to a waterjacketed ycondenser D, where the sublimed vapor condenses into the solid compound 10Itiiiill be observed that the transformingcompartment A', in which the electricallyheated diaphra ms are located,is protected l the electric diaphragms d d eing maintained at a vuniform temperature.

VI can/.produce aromatic ketonesby employing other aromaticfhydrocarbons or a mixture of hydrocarbons to `produce complex aromatic ketones, the aromatic hydrocarbons being vaporized directly or conveyed to the trans orming apparatus in vaporous' or gaseous form, and. I can employ other oxygen-yielding carbon compounds as oxidizing agents inste of carbon dioxid without departing from t e spirit of my invention, which consists in transforming aromatic hydrocarbons into their keto derivatives by the action of oxygen-yieldingV carbon compounds as oxidizing agents whi e maintaining the temperaD ture of the reacting ingredients below the -disso'ciating-point of the aromatic ketone desired. v

The dipentene which I employ in making the keto derivatiykfe of tetrahydromethylpropyl' benzene by the action ofa carbon.

Oxy-acid anhydrid, such as carbon dioxid heated to a suitable temperature, I prefer to obtain by heating oil of turpentine for several hours at an average temperature approximating 260"A under superatmospheric pressure, whereby the pinene content is transformed into dipentene which is readily collected by distillation.

It can be readily seen that the diaphragms d d in the transforming-compartment 'A' serve to ignite the mixture of vaporous or gaseousY hydrocarbon and -oxidizing agent, such as carbon dioxid, ((102,) as it comes in contact therewith and the excess of heat either absorbed therefrom or liberated by reaction is carried away from the heated diaphragms by the rapid-flowing gas or vapors admitted and the heat-absorbing gauze diaphragm d, the heated diaphragms serving to unite the aromatic hydrocarbon with the oxygen of the oxidizing agent, and the heat is abstracted so fast that the temperature is reduced below igniting-point. Any suitable heater `may be employed in connection with ymy apparatus in lieu of an electrical heater;

but I have found that an electrical heater is more easily controlled than a heater of any other form and that by its use the temperature may be contlelled and maintained with great uniformity and precision. I find it unnecessary to employ any temperature-indicat'ing device, as in practice the'thermal condition of the apparatus and its contents Will be Adetermined by the results attained.

The product of my process is a colorless semitransparent'substance, melting and sublimin without decomposition at 210 centigra e, having an aromatic camphorace'ous odor, and beingin its molten condition a ready solventfor pyroxylin. 4

A pharmacological examination of the product of this process reveals under the microscope a mass of iniinitesimal ellipsoidal crystals having elongatedand pointedends and being closely and concretely associated together, forming a tenacious material of somewhat brittle character, readily soluble in alcohol, small' particles of which also float upon water with a peculiarly rotating. and characteristic motion, which immediately ceases in the presence of 4,an oily substance.

Having now described my invention, what I claim as new, and desire to Secure by Letters Patent, is-

1. ,The process of making pyroxylin solvents and aromatic ketoncs, which consists in oxidizing aromatic hydrocarbons by the IOO action of an oxygen-yielding carbon com- I relied# 2` The process of making pyroxylin solvents and aromatic ketones, which consists in oxidizing aromatic hydrocarbons by the action of a carbon-oxid oxidizing agent at a reacting temperature, and maintaining the temperature below the dissociating-point of the product desired by refrigeration. 8. The process of making pyroxylin solvents and aromatic ketones, which consists densed product of hydrocarbon and carbon Oxy-acid anhydrid to the action of heat, and maintaining the temperature below -the dissociating-point ofthe product desired.

5. The process of making pyroxylin solvents and aromatic ketones, which consists in condensing and oxidizing aromatic hydrocarbons having a general formula of the ratio (H8)n by the action of a carbon Oxy-acid anhydrid while maintaining the temperature below the dissociating-point of the product desired.

6. The process of making a keto derivative of tetrahydro-methylpropyl benzene, which consists in oxidizing dipentene by the action of a carbon oxy-acid anhydrid while maintaining the temperature below the dissociating-p'oint ofthe product desired.

7. The process of making pyroxylin sol.- vents and aromatic ketones, which consists in oxidizing a vaporized or gaseous aromatic hydrocarbon by the action of an oxygenyielding carbon compound while maintaining the temperature below the dissociating-point of the product desired.

8. The process of making pyroxylin solvents and aromatic ketones, which consists in vaporizing an aromatic hydrocarbon and oxidizing the same by the action of an oxygen-yielding carbon compound whilemaintaining the temperature below the dissociatin -point ofthe product desired.

9. he process of making aromatic ke-l tones, which consists in exposin aromatic hydrocarbons to the action of car on dioxid at a reacting temperature, and maintaining the temperature below the dissociating-point of the product desired.

10'. The process of making aromatic, ketones, which consists in exposing dipentene to the laction of carbon dioxid at a reacting temperature, and maintaining the temperature below the dissociating-point of the product by refrigeration.

11. As a new article of manufacture a solid aromatic ketone consisting of a colorless, semitransparent substance small particles ot ellipsoidal crystals having pointed ends, the said crystals being concretely associated,readily soluble in alcohol and melting and subliming without decomposition at 210 centigrade, said ketone having an aromatic camphoraceous odor.

12. As a new article of manufacture, a solid aromatic ketone consisting of a colorless, sernitrans arent substance, melting and subliming witliout decomposition at 210 centigrade, having an aromatic` camphoraceous odor and being, in its molten state, a ready solvent for yroxylin.

In testimony W in presence of two witnesses.

HENRY SPENCER BLACKMORE. Witnesses:

H. N. JENKINS,

y C. C. WRIGHT.

composed of l ereof I alix my signature 

